DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes
This paper reports the synthesis, characterisation and DFT analysis of an N,O bidentate Schiff base, ((E)-(4-methoxybenzylimino)methyl)phenol, (L1c) and its Ni(II) and Pd(II) complexes. The structures were elucidated via elemental analysis, UV–Visible, NMR, IR and single crystal X-ray diffraction. C...
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| Format: | Article |
| Language: | English |
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Elsevier
2017-09-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535216302143 |
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| author | Amalina Mohd Tajuddin El Hassane Anouar Kalavathy Ramasamy Bohari M. Yamin Abdulrahman I. Alharthi Hadariah Bahron |
| author_facet | Amalina Mohd Tajuddin El Hassane Anouar Kalavathy Ramasamy Bohari M. Yamin Abdulrahman I. Alharthi Hadariah Bahron |
| author_sort | Amalina Mohd Tajuddin |
| collection | DOAJ |
| description | This paper reports the synthesis, characterisation and DFT analysis of an N,O bidentate Schiff base, ((E)-(4-methoxybenzylimino)methyl)phenol, (L1c) and its Ni(II) and Pd(II) complexes. The structures were elucidated via elemental analysis, UV–Visible, NMR, IR and single crystal X-ray diffraction. Complexation of L1c with Ni(II) and Pd(II) was observed to induce different degrees of bathochromic effect on n → π∗ and π → π∗ electronic transitions. A comparison of the experimental data of UV–Visible, NMR, IR and X-ray with those calculated using DFT and TD-DFT methods where five hybrid functionals were tested in gas, IEF-PCM and SS-PCM models was also carried out. The results show that the reproduction of maximum absorption bands n → π∗ and π → π∗ is strongly related to the tested hybrid functionals and solvatochromic effects. Relatively good concordance was obtained between experimental and calculated NMR chemical shifts, IR and X-ray parameters. A bioactivity evaluation against HCT116 and Escherichia coli displayed that the parent ligand L1c is a more superior anticancer and antibacterial agent than the positive controls of 5FU and gentamicin respectively. However, both complexes showed poor activity as anticancer agent and no activity observed against tested bacteria. |
| first_indexed | 2024-12-10T15:53:59Z |
| format | Article |
| id | doaj.art-f56d27e63dae4aa8904498cb3af9cab2 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-10T15:53:59Z |
| publishDate | 2017-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-f56d27e63dae4aa8904498cb3af9cab22022-12-22T01:42:43ZengElsevierArabian Journal of Chemistry1878-53522017-09-0110676978010.1016/j.arabjc.2016.11.005DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexesAmalina Mohd Tajuddin0El Hassane Anouar1Kalavathy Ramasamy2Bohari M. Yamin3Abdulrahman I. Alharthi4Hadariah Bahron5Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, MalaysiaCollege of Science and Humanities, The Department of Chemistry, Prince Sattam Bin Abdulaziz University, Al‐Kharj, Saudi ArabiaFaculty of Pharmacy, Universiti Teknologi MARA, 42300, Puncak Alam, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi, Selangor, MalaysiaCollege of Science and Humanities, The Department of Chemistry, Prince Sattam Bin Abdulaziz University, Al‐Kharj, Saudi ArabiaFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, MalaysiaThis paper reports the synthesis, characterisation and DFT analysis of an N,O bidentate Schiff base, ((E)-(4-methoxybenzylimino)methyl)phenol, (L1c) and its Ni(II) and Pd(II) complexes. The structures were elucidated via elemental analysis, UV–Visible, NMR, IR and single crystal X-ray diffraction. Complexation of L1c with Ni(II) and Pd(II) was observed to induce different degrees of bathochromic effect on n → π∗ and π → π∗ electronic transitions. A comparison of the experimental data of UV–Visible, NMR, IR and X-ray with those calculated using DFT and TD-DFT methods where five hybrid functionals were tested in gas, IEF-PCM and SS-PCM models was also carried out. The results show that the reproduction of maximum absorption bands n → π∗ and π → π∗ is strongly related to the tested hybrid functionals and solvatochromic effects. Relatively good concordance was obtained between experimental and calculated NMR chemical shifts, IR and X-ray parameters. A bioactivity evaluation against HCT116 and Escherichia coli displayed that the parent ligand L1c is a more superior anticancer and antibacterial agent than the positive controls of 5FU and gentamicin respectively. However, both complexes showed poor activity as anticancer agent and no activity observed against tested bacteria.http://www.sciencedirect.com/science/article/pii/S1878535216302143Schiff baseNi(II)Pd(II)HCT116Escherichia coliDFT |
| spellingShingle | Amalina Mohd Tajuddin El Hassane Anouar Kalavathy Ramasamy Bohari M. Yamin Abdulrahman I. Alharthi Hadariah Bahron DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes Arabian Journal of Chemistry Schiff base Ni(II) Pd(II) HCT116 Escherichia coli DFT |
| title | DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes |
| title_full | DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes |
| title_fullStr | DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes |
| title_full_unstemmed | DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes |
| title_short | DFT analysis and bioactivity of 2-((E)-(4-methoxybenzylimino)methyl)phenol and its Ni(II) and Pd(II) complexes |
| title_sort | dft analysis and bioactivity of 2 e 4 methoxybenzylimino methyl phenol and its ni ii and pd ii complexes |
| topic | Schiff base Ni(II) Pd(II) HCT116 Escherichia coli DFT |
| url | http://www.sciencedirect.com/science/article/pii/S1878535216302143 |
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